The Twenty Minute VC

Oana Olteanu: Why Founders Should Expect More From Their VCs | 20VC #950

Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. At SignalFire, Oana has led deals in the likes of Kurtosis, Enso, Kolena, Budibase, Plural, and Explosion. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana sourced Scale’s investments in Observe.ai, Flatfile, and Proscia. She was part of the deal teams for Honeycomb and AllyO (acquired by HireVue). She also supported existing portfolio companies such as Dialpad, Matillion, and BigID. Prior to Scale, Oana was an AI seed investor at SAP.io, SAP’s $35M seed fund, where she sourced the investments in Plum.io, Oto.ai, and Akorda. ---------------------------------------- Timestamps: 0:00 Who is Oana? 3:15 What are you running from/towards? 3:55 Schrödinger's VC 8:36 What should founders lean on their VCs for? 10:02 How to Give Negative Feedback 11:38 How to Scale like a Romanian 12:13 What do you do to bring your founders together? 13:31 Misalignments between VCs and Founders 15:30 The Main Ways VCs Behave Badly Today 16:15 Does Harry promote himself too much? 18:12 The Art of the Board Meeting 25:38 Hiring for Diversity 31:51 What changes do you want to see in VC? 32:22 What do you find hard about VC? 33:05 What compelled you to join SignalFire? 34:13 Oana’s Favourite Book 35:11 Most Underrated Angel Investor 35:21 What traps do most engineers fall into? 36:01 How Oana Learned to Drive a Tank 36:15 What do Oana’s parents think of her job? 36:42 Oana’s Biggest Win 37:55 What would you most like to change about VC? 39:09 What do you know now that you wish you’d know when you started? 39:55 Oana’s Most Recent Publicly Announced Investment ---------------------------------------- In Today’s Episode with Oana Olteanu We Discuss: 1.) From Tank Driving in Romania to VC’s Rising Star: How Oana made her way from driving tanks in Romania to becoming a VC? How did leaving Romania for Germany and then moving to the West Coast impact her mindset? What does Oana know now that she wishes she had known when she entered VC? 2.) How to Assess a VC: The Founders Guide: Pre-investment, how can founders know whether a VC can add value? What are the signs? What three core questions will reveal how much value a VC can add? Post-investment, what can founders do to extract the most value from their VCs? What should the founders ask their investors for help with? What should they do themselves? 3.) The VC-Founder Relationship: Oana has the highest founder NPS of any VC I have ever had on 20VC, what does Oana believe makes her founders rate her contribution so highly? What works? What does not? How does Oana give sometimes very hard feedback to founders but retain that relationship of trust and safety at the same time? What mistakes do other VCs make in giving feedback? What does Oana believe are the single biggest misalignment between VCs and founders? 4.) VCs Behaving Badly: 101 What are the single biggest ways Oana sees VCs behaving badly? How does Oana think founders expectations of the product of venture should change? Does Oana believe boards are valuable? What can be done to improve them? ---------------------------------------- #OanaOlteanu #HarryStebbings #20VC #signalfire #venturecapital

Harry StebbingshostOana Olteanuguest

Nov 18, 202241mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Raising the Bar: How Founders Should Demand More From VCs

Oana Olteanu, partner at SignalFire, shares her journey from a Romanian village to Silicon Valley VC and explains why founders should dramatically raise their expectations of investors. She introduces the idea of the “Schrödinger’s VC” — firms that loudly promise help but add no real value once on the cap table — and outlines how to identify and manage them. A large part of the conversation focuses on what great VC support actually looks like: concrete homework, proactive customer work, board effectiveness, and founder communities. Oana also discusses diversity in hiring, structural misalignments between founders and VCs, and how she’s trying to model a more founder-serving, low-ego approach to venture.

IDEAS WORTH REMEMBERING

5 ideas

Founders must actively screen VCs for real behavior, not promises.

During fundraising, watch what investors *do* in diligence—how they help, reference patterns, and how they talk about tough times in prior companies—rather than relying on marketing or brand alone.

Treat your VC like a resource you manage and assign homework to.

To avoid “useless” capital, founders should send materials with clear asks, give investors concrete projects (e.g., customer research, candidate sourcing, specific intros), and hold them accountable for outcomes.

Board meetings are only valuable if well-prepared and tightly run.

Great boards start with pre-calls, a focused written update (not a crutch slide deck), clear highlight/lowlight sections, and in-meeting time devoted to the meaty strategic issues—not rehashing what everyone already read.

You can and should engineer diversity; it’s not “too hard.”

If your candidate pool isn’t diverse, the problem is upstream: change recruiters if needed, reach out respectfully without reducing people to their gender, leverage dedicated communities (like Oana’s “She’s Ready to Dev”), and implement inclusive policies and benefits.

Founder–VC alignment improves when investors genuinely prioritize service over ego.

Misalignments (like VCs selling early for DPI) are real, but can be mitigated by transparent conversations, long-term thinking, and a default stance of optimizing for the company’s and founder’s success.

WORDS WORTH SAVING

5 quotes

I'm running from unfulfilled potential. I think there is nothing sadder than unfulfilled potential.

— Oana Olteanu

Schrödinger's VC is what I call a VC who preaches a lot of help, especially before winning a deal. But then if you ask the founders, they will tell you they added no value.

— Oana Olteanu

While a VC cannot play the chess game for you and move the pieces, they have seen a lot more games and therefore they can advise from near the chessboard.

— Oana Olteanu

You cannot hire diverse people if they are not even in your candidate pool.

— Oana Olteanu

I don't like to work with jerks. You can be amazingly smart, but you also have to actually want to build a healthy culture in your company.

— Oana Olteanu

Oana’s unconventional path into venture and immigrant backgroundThe concept of “Schrödinger’s VC” and how to evaluate investor value-addEffective founder–VC collaboration, including homework, accountability, and feedbackBoard dynamics: preparing, running, and debriefing board meetingsFounder–VC alignment and misalignment (liquidity needs, ego vs service)Diversity in tech hiring and building inclusive, attractive workplacesOana’s investing style, portfolio support, and views on venture culture

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